NPASS Compound

Natural Product: NPC61967

Natural Product ID	NPC61967
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ohchinin Acetate
IUPAC Name	n.a.
Synonyms	Ohchinin Acetate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1774399
PubChem CID	52952322
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 91 97 0 0 0 0 0 0 0 0999 V2000 -1.3358 3.0078 5.3725 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2122 2.2930 4.1685 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3543 1.2442 3.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3240 0.9979 5.0646 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0733 0.3935 2.8772 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5494 0.7129 1.4868 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0063 1.9689 0.8896 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3300 3.0885 1.8564 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3519 1.7127 0.1970 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5270 0.3863 -0.2160 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4175 -0.5186 0.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1533 -0.1012 1.1721 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5838 -1.9044 -0.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4864 -2.6846 0.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7315 -4.0760 0.0173 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7193 -4.8187 0.6593 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0023 -6.1226 0.3733 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2601 -6.7483 -0.6189 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2723 -6.0532 -1.2814 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0113 -4.7162 -0.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7980 2.7610 -0.7302 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8178 3.5752 -1.4840 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5407 3.6895 -0.9047 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8524 2.4391 -0.1907 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3106 2.6094 0.0626 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8448 1.2812 0.4668 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9761 0.3876 1.2529 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6891 0.0973 2.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1198 -0.9208 0.4851 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9425 -2.2343 0.4765 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3359 -2.9551 1.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4492 -2.8569 -0.7529 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3863 -1.7844 -1.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6701 -0.5331 -0.8322 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4243 0.5589 -0.6051 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5207 -3.4155 -1.6867 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5213 -4.7448 -2.1115 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4888 -4.9000 -3.0124 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1053 -3.7541 -3.1354 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4692 -2.8439 -2.3702 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7710 3.0801 -1.1425 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 3.5009 -1.9364 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8182 5.0015 -0.2840 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7216 3.2096 -2.8585 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0573 4.0447 -3.9048 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4738 5.2043 -3.5826 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9613 3.6723 -5.3401 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5457 2.6843 6.1116 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2042 4.0976 5.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3365 2.8548 5.8067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2313 -0.6728 3.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0920 0.3903 2.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0093 -0.0990 0.8861 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4927 3.7554 2.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0504 3.7937 1.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9834 2.7810 2.6967 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0805 1.7433 1.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9715 -2.2984 -0.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0921 -2.2179 1.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2726 -4.2915 1.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7865 -6.6863 0.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5024 -7.7884 -0.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7162 -6.5693 -2.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2365 -4.2105 -1.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4523 2.2688 -1.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 3.4278 -0.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2070 4.6371 -1.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 1.6229 -0.9767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4624 3.3065 0.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7745 1.5115 1.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5559 -0.5799 2.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1273 -0.5152 3.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2092 0.9757 2.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3478 -4.0474 1.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9375 -2.8004 2.5776 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2814 -2.6716 1.8126 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1683 -3.6594 -0.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3752 -1.7988 -0.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5276 -1.8425 -2.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8811 -0.4030 -1.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1878 -5.5455 -1.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2496 -5.8468 -3.5127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1214 -1.8116 -2.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8757 4.4426 -2.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3351 2.7145 -2.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6130 5.0722 0.4480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1075 5.5690 0.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1752 5.6877 -1.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0364 3.8153 -5.7603 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6509 4.3362 -5.9073 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3689 2.6364 -5.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 9 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 32 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 1 0 25 41 1 0 41 42 1 0 23 43 1 1 22 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 27 6 1 0 34 29 1 0 40 36 2 0 24 7 1 0 35 26 1 0 20 15 1 0 42 23 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 5 52 1 0 6 53 1 6 8 54 1 0 8 55 1 0 8 56 1 0 9 57 1 1 13 58 1 0 14 59 1 0 16 60 1 0 17 61 1 0 18 62 1 0 19 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 6 24 68 1 6 25 69 1 1 26 70 1 1 28 71 1 0 28 72 1 0 28 73 1 0 31 74 1 0 31 75 1 0 31 76 1 0 32 77 1 1 33 78 1 0 33 79 1 0 34 80 1 6 37 81 1 0 38 82 1 0 40 83 1 0 42 84 1 0 42 85 1 0 43 86 1 0 43 87 1 0 43 88 1 0 47 89 1 0 47 90 1 0 47 91 1 0 M END

Standard InCHIKey	JYFHWXOCTSBEPC-CUNMOGCISA-N
Standard InCHI	InChI=1S/C38H44O9/c1-21-25(24-14-15-43-19-24)16-26-32(21)38(5)27(17-31(41)42-6)37(4)29(47-30(40)13-12-23-10-8-7-9-11-23)18-28(45-22(2)39)36(3)20-44-33(34(36)37)35(38)46-26/h7-15,19,25-29,33-35H,16-18,20H2,1-6H3/b13-12+/t25-,26-,27-,28-,29+,33-,34+,35-,36-,37+,38-/m1/s1
SMILES	COC(=O)C[C@@H]1[C@@]2(C)[C@@H](OC(=O)/C=C/c3ccccc3)C[C@H]([C@@]3([C@@H]2[C@H]([C@@H]2[C@@]1(C)C1=C(C)[C@@H](C[C@H]1O2)c1ccoc1)OC3)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	644.3	Volume:	658.656 ? Van der Waals volume.
Dense:	0.978	LogP:	4.515 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.755 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.751 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	37.0
TPSA:	110.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.154	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.4	Fsp³:	0.553
MCE-18:	156.356 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.991	Fluc inhibitor:	0.318 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.064 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.061	Promiscuous compounds:	0.19

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.028	MDCK Permeability:	-4.668
Pgp-inhibitor:	0.999	Pgp-substrate:	0.028
PAMPA:	0.093 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.595	30% Bioavailability (F30%):	0.84
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087	MRP1:	0.982
Plasma Protein Binding (PPB):	95.392%	Volume Distribution (VD):	-0.188
Fu:	4.335% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.702	BCRP inhibitor:	0.038
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.283 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.821

Half-life (T1/2):

0.791

ADMET: Toxicity

hERG Blockers:	0.302	hERG Blockers (10um):	0.392
Human Hepatotoxicity (H-HT):	0.783	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.835	Rat Oral Acute Toxicity:	0.854
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	0.994
Carcinogencity:	0.596	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.683
Drug-induced Neurotoxicity:	0.973	Ototoxicity:	0.682
Hematotoxicity:	0.476	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.984	RPMI-8226 Immunitoxicity:	0.311
A549 Cytotoxicity:	0.844	Hek293 Cytotoxicity:	0.674
BCF:	0.897 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.955 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.931 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.34 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s12038-008-0027-6]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37151484]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	3
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	9900.0	nM	PMID[21381696]
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[21381696]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[21381696]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[21381696]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC61967 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	12026
0.1-0.2	35278
0.2-0.3	2341
0.3-0.4	171
0.4-0.5	19
0.5-0.6	9
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7931	Intermediate Similarity	NPC322546
0.7841	Intermediate Similarity	NPC308205
0.7396	Intermediate Similarity	NPC475237
0.7363	Intermediate Similarity	NPC488535
0.6989	Remote Similarity	NPC62692
0.6966	Remote Similarity	NPC604850
0.6889	Remote Similarity	NPC182427
0.6813	Remote Similarity	NPC29695
0.6735	Remote Similarity	NPC27541
0.6633	Remote Similarity	NPC126984
0.6061	Remote Similarity	NPC214495
0.6061	Remote Similarity	NPC470119
0.6022	Remote Similarity	NPC291150
0.5895	Remote Similarity	NPC116717
0.5825	Remote Similarity	NPC475641
0.5789	Remote Similarity	NPC5180
0.5588	Remote Similarity	NPC475226
0.5481	Remote Similarity	NPC118086
0.5347	Remote Similarity	NPC475066
0.5152	Remote Similarity	NPC601664
0.5051	Remote Similarity	NPC470118
0.5047	Remote Similarity	NPC608643

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC61967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3075
0.1-0.2	6027
0.2-0.3	48
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data